Method for producing trans-1-chloro-3,3,3-trifluoropropene

Abstract

A method for producing 1-chloro-3,3,3-trifluoropropene efficiently from an intermediate product having a low reactivity is provided. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising reacting a halogenated hydrocarbon compound having 3 carbon atoms represented by Formula (1) shown below in a gas phase with hydrogen fluoride in the presence of chlorine is provided. C 3 H X Cl Y F Z (1) wherein X is 2 or 3; and when X=2, Y is an integer from 1 to 4, Z is an integer from 0 to 3, and Y+Z=4; and when X=3, Y is an integer from 1 to 5, Z is an integer from 0 to 4, and Y+Z=5; provided that Formula (1) shown above represents a halogenated hydrocarbon compound having 3 carbon atoms excluding trans-1-chloro-3,3,3-trifluoropropene.

What is claimed is: 
     
       1. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising:
 reacting a starting material containing a plurality of halogenated hydrocarbon compounds, each having 3 carbon atoms of Formula (1):
   C 3 H X Cl Y F Z   (1)
 
 
 in a gas phase with hydrogen fluoride in the presence of chlorine as a catalyst, 
 wherein X is 2 or 3; and when X=2, Y is an integer from 1 to 4, Z is an integer from 0 to 3, and Y+Z=4; and when X=3, Y is an integer from 1 to 5, Z is an integer from 0 to 4, and Y+Z=5; provided that Formula (1) shown above represents a halogenated hydrocarbon compound having 3 carbon atoms excluding trans-1-chloro-3,3,3-trifluoropropene. 
 
     
     
       2. The production method according to  claim 1  wherein a hydrocarbon compound having 3 carbon atoms of Formula (2):
   C 3 H V F W   (2)
 
 is further added and reacted in a gas phase with hydrogen fluoride in the presence of chlorine, 
 wherein when V+W=8, then V is an integer from 0 to 8; when V+W=6, then V is an integer from 0 to 6; and when V+W=4, then V is an integer from 0 to 4. 
 
     
     
       3. The production method according to  claim 1  wherein each of the plurality of halogenated hydrocarbon compounds having 3 carbon atoms is selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,1,1,3-tetrachloro-3-fluoropropane (241fb), 1,3,3-trichloro-3-fluoropropene (1231zd), 1,3,3-trichloro-1-fluoropropene (1231zb), 3,3,3-trichloro-1-fluoropropene (1231ze), 1,1,3-trichloro-3-fluoropropene (1231za), 1,3,3-trichloro-1,1-difluoropropane (242fa), 1,1,3-trichloro-1,3-difluoropropane (242fb), 1,3-dichloro-3,3-difluoropropene (1232zd), 3,3-dichloro-1,3-difluoropropene (1232ze), 3,3-dichloro-1,1-difluoropropene (1232zc), 1,3-dichloro-1,3-difluoropropene (1232zb), cis-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), 3,3-dichloro-1,1,1-trifluoropropane (243fa) and 3-chloro-1,1,1,3-tetrafluoropropane (244fa). 
     
     
       4. The production method according to  claim 1  wherein the reaction temperature is from 150° C. to 600° C. 
     
     
       5. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising reacting a starting material containing a plurality of halogenated hydrocarbon compounds, each selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,1,1,3,3-pentachloropropane (240fa), 1,3,3-trichloro-1,1-difluoropropane (242fa) in a gas phase with hydrogen fluoride as a catalyst at a temperature from 150° C. to 600° C. in the presence of chlorine as a catalyst. 
     
     
       6. The production method according to  claim 5  wherein a hydrocarbon compound having 3 carbon atoms of Formula (3):
   C 3 H V F W   (3)
 
 is further added and reacted in a gas phase with hydrogen fluoride in the presence of chlorine, 
 wherein when V+W=8, then V is an integer from 0 to 8; when V+W=6, then V is an integer from 0 to 6; and when V+W=4, then V is an integer from 0 to 4. 
 
     
     
       7. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising:
 Step (A) for reacting 1,1,1,3,3-pentachloropropane (240fa) with hydrogen fluoride, and 
 Step (B) for reacting a plurality of intermediate products, each obtained in the Step (A) in a gas phase with hydrogen fluoride at a temperature from 150° C. to 600° C. in the presence of chlorine as a catalyst to obtain trans-1-chloro-3,3,3-trifluoropropene. 
 
     
     
       8. The production method according to  claim 7  wherein a hydrocarbon compound having 3 carbon atoms of Formula (4):
   C 3 H V F W   (4)
 
 is further added and reacted in a gas phase with hydrogen fluoride in the presence of chlorine, 
 wherein when V+W=8, then V is an integer from 0 to 8; when V+W=6, then V is an integer from 0 to 6; and when V+W=4, then V is an integer from 0 to 4. 
 
     
     
       9. The production method according to  claim 7  wherein
 the Step (A) is conducted under a catalyst-free condition in a liquid phase to recover a reaction product gas containing trans-1-chloro-3,3,3-trifluoropropene, and 
 the reaction fluid of the Step (A) is recovered and the intermediate products contained in said reaction fluid are employed in the Step (B). 
 
     
     
       10. The production method according to  claim 9  wherein
 the 1,1,1,3,3-pentachloropropane and the hydrogen fluoride are introduced continuously or intermittently to the Step (A), and 
 the reaction product gas and the reaction fluid are recovered continuously or intermittently. 
 
     
     
       11. The production method according to  claim 7  wherein each of the plurality of intermediate products is selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,1,1,3-tetrachloro-3-fluoropropane (241fb), 1,3,3-trichloro-3-fluoropropene (1231zd), 1,3,3-trichloro-1-fluoropropene (1231zb), 3,3,3-trichloro-1-fluoropropene (1231ze), 1,1,3-trichloro-3-fluoropropene (1231za), 1,3,3-trichloro-1,1-difluoropropane (242fa), 1,1,3-trichloro-1,3-difluoropropane (242fb), 1,3-dichloro-3,3-difluoropropene (1232zd), 3,3-dichloro-1,3-difluoropropene (1232ze), 3,3-dichloro-1,1-difluoropropene (1232zc), 1,3-dichloro-1,3-difluoropropene (1232zb), cis-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), 3,3-dichloro-1,1,1-trifluoropropane (243fa), 1,3-dichloro-1,1,3-trifluoropropane (243fb), 1,1-dichloro-1,3,3-trifluoropropane (243fc), 1-chloro-1,1,3,3-tetrafluoropropane (244fb) and 3-chloro-1,1,1,3-tetrafluoropropane (244fa). 
     
     
       12. The production method according to  claim 7  wherein at least one of the plurality of intermediate products comprises 1,3,3-trichloro-1,1-difluoropropane (242fa). 
     
     
       13. The production method according to  claim 7  wherein the reaction temperature of the Step (B) is from 150° C. to 500° C. 
     
     
       14. The production method according to  claim 7  wherein unreacted intermediate products are recovered and employed in the Step (B). 
     
     
       15. The production method according to  claim 7  wherein cis-1-chloro-3,3,3-trifluoropropene is obtained in the Step (B) together with trans-1-chloro-3,3,3-trifluoropropene. 
     
     
       16. The production method according to  claim 15  wherein cis-1-chloro-3,3,3-trifluoropropene obtained is subjected as intermediate products to the Step (B). 
     
     
       17. The production method according to  claim 15  wherein cis-1-chloro-3,3,3-trifluoropropene obtained is heated at a temperature from 150° C. to 600° C. to obtain trans-1-chloro-3,3,3-trifluoropropene. 
     
     
       18. The production method according to  claim 2  wherein the hydrocarbon compound having 3 carbon atoms is at least one selected from the group consisting of 1,1,1,3,3-pentafluoropropane (245fa), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), cis-1,3,3,3-tetrafluoropropene (1234ze(Z)), 1,1,3,3-tetrafluoropropene (1234zc), and 3 ,3,3-trifluoropropine. 
     
     
       19. The production method according to  claim 6  wherein the hydrocarbon compound having 3 carbon atoms is at least one selected from the group consisting of 1,1,1,3,3-pentafluoropropane (245fa), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), cis-1,3,3,3-tetrafluoropropene (1234ze(Z)), 1,1,3,3-tetrafluoropropene (1234zc), and 3,3,3-trifluoropropine. 
     
     
       20. The production method according to  claim 8  wherein the hydrocarbon compound having 3 carbon atoms is at least one selected from the group consisting of 1,1,1,3,3-pentafluoropropane (245fa), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), cis-1,3,3,3-tetrafluoropropene (1234ze(Z)), 1,1,3,3-tetrafluoropropene (1234zc), and 3,3,3-trifluoropropine.